KR880001668A - 페넴의 합성 방법 - Google Patents

페넴의 합성 방법 Download PDF

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Publication number
KR880001668A
KR880001668A KR1019870008186A KR870008186A KR880001668A KR 880001668 A KR880001668 A KR 880001668A KR 1019870008186 A KR1019870008186 A KR 1019870008186A KR 870008186 A KR870008186 A KR 870008186A KR 880001668 A KR880001668 A KR 880001668A
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KR
South Korea
Prior art keywords
compound
formula
alkyl
solvent
cis
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KR1019870008186A
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English (en)
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KR890004581B1 (ko
Inventor
엘리자베스 브라이티 캐더린
Original Assignee
월리암 데이비스 헌
화이자 인코포레이티드
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Application filed by 월리암 데이비스 헌, 화이자 인코포레이티드 filed Critical 월리암 데이비스 헌
Publication of KR880001668A publication Critical patent/KR880001668A/ko
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Publication of KR890004581B1 publication Critical patent/KR890004581B1/ko

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • C07D499/88—Compounds with a double bond between positions 2 and 3 and a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Electric Double-Layer Capacitors Or The Like (AREA)
  • Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Control Of El Displays (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Paints Or Removers (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Mechanical Pencils And Projecting And Retracting Systems Therefor, And Multi-System Writing Instruments (AREA)
  • Steroid Compounds (AREA)
  • Pens And Brushes (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

내용 없음

Description

페넴의 합성 방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (10)

  1. (a) 일반식(Ⅲ)의 화합물을 반응-불활성 용매중, -80내지 40℃에서 염기로 처리하여 일반식(Ⅰ)의 화합물 및 일반식(Ⅱ)의 화합물을 함유하는 혼합물을 수득하고,
    (b) 일반식(Ⅱ)의 화합물을 동일한 용매 또는 제2의 반응-불활성 용매 중, -50내지 40℃에서 (P2O)3P또는 (R3)3P(여기에서, 각각의 R2는 동일하거나 상이하며(C1내지 C4) 알킬중에서 선택되며 각각의 R3는 동일하거나 상이하며 (C1내지 C4)알킬 및 페닐 중에서 선택된다)로 탈황화시켜 일반식(Ⅰ)의 화합물을 추가로 생성시킴을 특징으로 하여, 일반식(Ⅰ)의 화합물을 제조하는 방법.
    상기식에서, R은 (C1내지 C5)알킬 또는이며 R1은 통상의 하이드록시 보호그룹이다.
  2. 제2항에 있어서, R1이 t-부틸디메틸실릴이며 R이 t-부틸 또는 시스인 방법.
  3. 제2항에 있어서, 단계(a)에서의 염기가 1,8-디아자비사이클로 [5,4,0] 운데크-7-엔인 방법.
  4. 제2항에 있어서, 단계 (a)에서의 용매가 아세토니트릴인 방법.
  5. 제2항에 있어서, 단계(b)에서의 시약이 트리페닐포스핀인 방법.
  6. 제3항에 있어서, R이 시스이며, 단계(b)에서의 용매가 아세토니트릴이고 단계(b)에서의 시약이 트리페닐포스핀인 방법.
  7. 제1항에 있어서, 다음 일반식의 화합물이 메탄설포닐 클로라이드 및 3급 아민을 작용시키는 단계를 추가로 포함하여 일반식(Ⅰ)의 화합물을 제조하는 방법.
    (Ⅲ)
    상기식에서, R 및 R1은 제 1항에서 정의한 바와 같다.
  8. 다음 일반식의 화합물.
    (Ⅲ)
    상기식에서 R은 (C1내지 C5)알킬이거나이며 R1은 통상의 하이드록시 보호그룹이다.
  9. 제8항에 있어서, R1이 t-부틸디메틸 실릴이며 R이 t-부틸인 화합물.
  10. 제8항에 있어서, R1이 t-부틸디메틸 실릴이며 R이 시스인 화합물.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019870008186A 1986-07-29 1987-07-28 페넴의 합성방법 KR890004581B1 (ko)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US06/891,493 US4695626A (en) 1986-07-29 1986-07-29 1-aza-4,5-dithiabicyclo [4.2.0] oct-2-en-8-one-2 carboxylate esters
US891.493 1986-07-29
US891439 1997-07-10

Publications (2)

Publication Number Publication Date
KR880001668A true KR880001668A (ko) 1988-04-26
KR890004581B1 KR890004581B1 (ko) 1989-11-16

Family

ID=25398284

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1019870008186A KR890004581B1 (ko) 1986-07-29 1987-07-28 페넴의 합성방법

Country Status (18)

Country Link
US (2) US4695626A (ko)
EP (1) EP0255307B1 (ko)
JP (1) JPH0737462B2 (ko)
KR (1) KR890004581B1 (ko)
AT (1) ATE70064T1 (ko)
AU (1) AU583465B2 (ko)
CA (1) CA1285275C (ko)
DE (1) DE3774954D1 (ko)
DK (1) DK170169B1 (ko)
ES (1) ES2038665T3 (ko)
FI (1) FI87651C (ko)
GR (1) GR3003660T3 (ko)
HU (1) HU198068B (ko)
IE (1) IE60029B1 (ko)
IL (1) IL83304A (ko)
NZ (1) NZ221201A (ko)
PT (1) PT85407B (ko)
ZA (1) ZA875541B (ko)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU563157B2 (en) * 1982-12-08 1987-07-02 Farmitalia Carlo Erba S.P.A. 2-thiacephems and (5r) penems derivatives
US4782145A (en) * 1986-06-02 1988-11-01 Pfizer Inc. Process for penem derivatives
US4751297A (en) * 1987-03-20 1988-06-14 Pfizer Inc. Method for preparation of azetidinone-1-oxoacetate by oxidation of the corresponding 2-hydroxyacetate
US5191077A (en) * 1987-05-11 1993-03-02 Pfizer Inc. Diastereomeric 5R,6S-6-(1R-hydroxyethyl)-2-(cis-1-oxo-3-thiolanylthio)-2-penem-3-carboxylic acids
WO1988008845A1 (en) * 1987-05-11 1988-11-17 Pfizer Inc. Diastereomeric 5r,6s-6-(1r-hydroxyethyl)-2-(cis-1-oxo-3-thiolanylthio)-2-penem-3-carboxylic acids
DE19512050A1 (de) * 1995-03-31 1996-10-02 Gimmy Lindomare Dr Vorrichtung zum Sichern von Schrauben vor unbefugtem Zugriff
MXPA06013412A (es) * 2004-05-19 2007-01-23 Maxygen Inc Polipeptidos de interferon-alfa y conjugados.
US7977078B2 (en) 2007-08-24 2011-07-12 Codexis, Inc. Ketoreductase polypeptides for the production of (R)-3-hydroxythiolane
EP3523309B1 (en) * 2016-10-10 2024-04-17 The Johns Hopkins University Antibacterial agents against d,d- and l,d-transpeptidases

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH541576A (de) * 1970-11-03 1973-09-15 Ciba Geigy Ag Verfahren zur Herstellung thiaheterocyclischer Verbindungen
EP0176064A1 (en) * 1980-11-06 1986-04-02 Hoechst Uk Limited Intermediates for the production of 7-oxo-4-thia-1-aza[3,2,0]heptane and 7-oxo-4-thia-1-aza[3,2,0]hept-2-ene derivatives
JPS57176988A (en) * 1981-04-09 1982-10-30 Sankyo Co Ltd Penam-3-carboxylic acid derivative and its preparation
AU563157B2 (en) * 1982-12-08 1987-07-02 Farmitalia Carlo Erba S.P.A. 2-thiacephems and (5r) penems derivatives
GB2131432B (en) * 1982-12-08 1986-10-15 Erba Farmitalia Preparation of (5r)-penem derivatives
EP0115308A3 (en) * 1983-01-25 1984-10-10 Merck & Co. Inc. 2-unsaturated alkylthio-pen-2-em-3-carboxylic acids and process for preparing substituted 2-thioxopenams and 2-substituted thiopenems
EP0130025B1 (en) * 1983-06-21 1987-07-08 Pfizer Inc. 2-alkylthiopenem derivatives
EP0132101A1 (en) * 1983-07-14 1985-01-23 Pfizer Inc. 2-Heterocycloalkylthiopenem derivatives

Also Published As

Publication number Publication date
CA1285275C (en) 1991-06-25
GR3003660T3 (ko) 1993-03-16
IE60029B1 (en) 1994-05-18
AU583465B2 (en) 1989-04-27
DE3774954D1 (de) 1992-01-16
KR890004581B1 (ko) 1989-11-16
IL83304A0 (en) 1987-12-31
JPS6341481A (ja) 1988-02-22
FI873290A (fi) 1988-01-30
FI87651B (fi) 1992-10-30
PT85407B (pt) 1990-04-30
NZ221201A (en) 1990-06-26
DK170169B1 (da) 1995-06-06
HUT45067A (en) 1988-05-30
IL83304A (en) 1992-06-21
HU198068B (en) 1989-07-28
DK392287A (da) 1988-01-30
EP0255307B1 (en) 1991-12-04
US4782146A (en) 1988-11-01
PT85407A (en) 1987-08-01
ZA875541B (en) 1989-03-29
DK392287D0 (da) 1987-07-28
AU7618787A (en) 1988-02-04
US4695626A (en) 1987-09-22
ES2038665T3 (es) 1993-08-01
FI873290A0 (fi) 1987-07-28
IE872046L (en) 1988-01-29
JPH0737462B2 (ja) 1995-04-26
FI87651C (fi) 1993-02-10
EP0255307A1 (en) 1988-02-03
ATE70064T1 (de) 1991-12-15

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